Reducing properties of 1,2-dipyridyl-1,2-disodioethanes: chemical validation of theoretical and electrochemical predictions?

RSC Advances Pub Date: 2016-05-04 DOI: 10.1039/C6RA03303B

Abstract

The reducing properties of highly delocalized radical anions and dianions of 1,2-di(hetero)arylethenes were investigated by theoretical calculations at the PBE0/6-311+G(d,p)/IEFPCM level. The results correlated nicely with the reduction potentials determined by analysis of the voltammetric curves for the reduction of the parent alkenes, and this allowed a reliable scale for their relative reducing strength to be established. In full agreement with calculations and electrochemical results, use of the appropriate 1,2-dipyridyl-1,2-disodioethane as a base led to the successful α-alkylation of bromophenylacetic acids under mild reaction conditions, thus avoiding the competitive reductive cleavage of aromatic C–Br bonds.

Graphical abstract: Reducing properties of 1,2-dipyridyl-1,2-disodioethanes: chemical validation of theoretical and electrochemical predictions
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